NPASS Compound

Natural Product: NPC244640

Natural Product ID	NPC244640
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Macrocarpal A
IUPAC Name	5-[(1R)-1-[(1aR,4R,4aR,7S,7aS,7bR)-4-hydroxy-1,1,4,7-tetramethyl-1a,2,3,4a,5,6,7a,7b-octahydrocyclopropa[h]azulen-7-yl]-3-methylbutyl]-2,4,6-trihydroxybenzene-1,3-dicarbaldehyde
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL396609
PubChem CID	454457
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0001781] Aromadendrane sesquiterpenoids [CHEMONTID:0003562] 5,10-cycloaromadendrane sesquiterpenoids

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 74 77 0 0 0 0 0 0 0 0999 V2000 2.1432 -4.0801 -0.6033 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7583 -3.0901 0.2800 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2796 -3.3892 0.3472 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5248 -1.6489 0.1252 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2584 -0.9538 0.2807 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5175 0.5150 -0.0107 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7097 0.8914 -1.3151 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9850 2.2285 -1.6447 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2057 2.6548 -3.0151 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3450 3.0504 -3.8151 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0631 3.1737 -0.6627 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8740 2.8189 0.6426 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9612 3.8379 1.6671 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0648 4.0739 2.2010 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6042 1.4904 0.9407 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4208 1.1721 2.2725 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3374 4.5231 -0.9646 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6572 0.0370 -2.3977 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0807 -1.4439 -0.0144 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3694 -1.8936 -1.4119 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5875 -2.4984 0.9345 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0558 -1.6660 2.1423 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9454 -0.7265 1.4252 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1325 -0.3073 0.2174 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1551 -0.2368 -0.8591 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1892 0.7333 -0.5707 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9871 1.9159 0.2587 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3854 1.7443 1.6071 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5228 0.3738 2.1958 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8974 0.4220 3.5698 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9123 0.1962 2.4424 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3633 0.7484 -1.8775 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4223 1.8968 -2.1084 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0944 0.3381 -3.1442 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6284 -5.0777 -0.4249 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3789 -3.7639 -1.6764 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0758 -4.2223 -0.5235 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4446 -3.3535 1.3515 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3953 -4.3947 0.7509 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6840 -3.2499 -0.6707 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7142 -2.6309 1.0164 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2509 -1.1845 0.9076 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1003 -1.2580 -0.8090 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2031 -0.8683 1.4749 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2352 2.6253 -3.3827 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1001 4.3795 1.9629 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1855 0.7515 2.7847 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2850 4.8325 -0.7175 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1918 0.1275 -3.2295 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8161 -1.0874 -2.0669 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1525 -2.6835 -1.3874 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4597 -2.3599 -1.9619 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5184 -2.9451 0.5017 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1204 -3.2518 1.2550 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6596 -2.4066 2.7440 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2363 -1.2685 2.7169 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8287 -1.3749 1.0879 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5966 0.6159 0.3657 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5612 -1.2799 -1.0911 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2661 0.4083 -0.7474 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0125 2.3799 0.4370 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4626 2.7518 -0.2447 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3093 2.0115 1.6357 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8617 2.4345 2.3439 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9896 1.0539 3.5223 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5967 0.9698 4.2714 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6529 -0.5783 3.9791 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2631 -0.2942 1.6504 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8447 2.2107 -1.2472 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6886 1.5123 -2.8682 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9069 2.7682 -2.5773 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5688 -0.6365 -2.9803 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9002 1.0720 -3.3310 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3695 0.3640 -3.9573 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 1 0 9 10 2 0 8 11 2 0 11 12 1 0 12 13 1 0 13 14 2 0 12 15 2 0 15 16 1 0 11 17 1 0 7 18 1 0 5 19 1 0 19 20 1 6 19 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 29 31 1 1 26 32 1 0 32 33 1 0 32 34 1 0 15 6 1 0 24 19 1 0 32 25 1 0 29 23 1 0 1 35 1 0 1 36 1 0 1 37 1 0 2 38 1 0 3 39 1 0 3 40 1 0 3 41 1 0 4 42 1 0 4 43 1 0 5 44 1 1 9 45 1 0 13 46 1 0 16 47 1 0 17 48 1 0 18 49 1 0 20 50 1 0 20 51 1 0 20 52 1 0 21 53 1 0 21 54 1 0 22 55 1 0 22 56 1 0 23 57 1 6 24 58 1 1 25 59 1 6 26 60 1 6 27 61 1 0 27 62 1 0 28 63 1 0 28 64 1 0 30 65 1 0 30 66 1 0 30 67 1 0 31 68 1 0 33 69 1 0 33 70 1 0 33 71 1 0 34 72 1 0 34 73 1 0 34 74 1 0 M END

Standard InCHIKey	IBLPTYJTKWQCDX-MOTAWSDJSA-N
Standard InCHI	InChI=1S/C28H40O6/c1-14(2)11-19(20-24(32)15(12-29)23(31)16(13-30)25(20)33)27(5)9-7-18-22(27)21-17(26(21,3)4)8-10-28(18,6)34/h12-14,17-19,21-22,31-34H,7-11H2,1-6H3/t17-,18-,19+,21-,22-,27-,28-/m1/s1
SMILES	CC(C)C[C@@H](c1c(c(C=O)c(c(C=O)c1O)O)O)[C@@]1(C)CC[C@@H]2[C@@H]1[C@H]1[C@@H](CC[C@@]2(C)O)C1(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	472.28	Volume:	498.177 ? Van der Waals volume.
Dense:	0.948	LogP:	5.189 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.03 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.083 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	21.0
TPSA:	115.06 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	4.0	Rings:	4.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.412	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.006	Fsp³:	0.714
MCE-18:	114.125 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.62	Fluc inhibitor:	0.017 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.047 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.007 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.276	Promiscuous compounds:	0.408

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.737	MDCK Permeability:	-4.948
Pgp-inhibitor:	0.676	Pgp-substrate:	0.005
PAMPA:	0.528 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.011	30% Bioavailability (F30%):	0.096
50% Bioavailability (F50%):	0.599

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.05	MRP1:	0.836
Plasma Protein Binding (PPB):	98.251%	Volume Distribution (VD):	-0.191
Fu:	1.38% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.991
OATP1B3 inhibitor:	0.861	BCRP inhibitor:	0.275
BSEP inhibitor:	0.964

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.082	CYP2C19-substrate:	0.393
CYP2C9-inhibitor:	0.013	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.996	CYP3A4-substrate:	0.386
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.73
HLM stability:	0.005 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

6.813

Half-life (T1/2):

1.319

ADMET: Toxicity

hERG Blockers:	0.009	hERG Blockers (10um):	0.197
Human Hepatotoxicity (H-HT):	0.443	Drug-induced Liver Injury (DILI):	0.023
AMES Toxicity:	0.16	Rat Oral Acute Toxicity:	0.193
Maximum Recommended Daily Dose:	0.5	Skin Sensitization:	0.96
Carcinogencity:	0.226	Eye Corrosion:	0.559
Eye Irritation:	0.991	Respiratory Toxicity:	0.809
Drug-induced Neurotoxicity:	0.015	Ototoxicity:	0.31
Hematotoxicity:	0.063	Drug-induced Nephrotoxicity:	0.301
Genotoxicity:	0.215	RPMI-8226 Immunitoxicity:	0.104
A549 Cytotoxicity:	0.694	Hek293 Cytotoxicity:	0.484
BCF:	2.065 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	5.014 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.807 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	6.17 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1002/elan.200403102]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.foodchem.2012.02.124]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[11077184]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[17328234]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	n.a.	fruit	n.a.	PMID[18020353]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flower buds	n.a.	n.a.	PMID[18321056]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	flower	n.a.	PMID[21804227]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	flower buds	Henan province, China	2005-MAY	PMID[21942812]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	flower bud	n.a.	PMID[21942812]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22934600]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23265495]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[23678820]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flower buds	n.a.	n.a.	PMID[24279769]
NPO7175	Eucalyptus robusta	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27142786]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[30543429]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[30848923]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[35108453]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36903935]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37047195]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37179510]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38263385]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38380569]
NPO7175	Eucalyptus robusta	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39064968]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39592457]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[8864235]
NPO7175	Eucalyptus robusta	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7175	Eucalyptus robusta	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7175	Eucalyptus robusta	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7175	Eucalyptus robusta	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7175	Eucalyptus robusta	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Activity	1
Ratio	3
MIC	12
Inhibition	3
IC50	2

Activity Type	# Activity
Cell line	3
Organism	12
Single protein	1
Others	3
Non-molecular	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT21657	Single protein	DNA topoisomerase I	Bos taurus	Activity	=	34.0	%	PMID[30543429]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT492	Cell line	Caco-2	Homo sapiens	Ratio	=	1.02	n.a.	PMID[17118653]
NPT492	Cell line	Caco-2	Homo sapiens	Ratio	=	0.98	n.a.	PMID[17118653]
NPT492	Cell line	Caco-2	Homo sapiens	Ratio	=	1.27	n.a.	PMID[17118653]
NPT878	Organism	Streptococcus mutans	Streptococcus mutans	MIC	=	0.78	ug.mL-1	PMID[8864235]
NPT4829	Organism	Prevotella melaninogenica	Prevotella melaninogenica	MIC	=	0.78	ug.mL-1	PMID[8864235]
NPT1128	Organism	Prevotella intermedia	Prevotella intermedia	MIC	=	0.39	ug.mL-1	PMID[8864235]
NPT1484	Organism	Fusobacterium nucleatum	Fusobacterium nucleatum	MIC	=	6.25	ug.mL-1	PMID[8864235]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	<	10000.0	nM	PMID[27142786]
NPT5408	Organism	Capnocytophaga ochracea	Capnocytophaga ochracea	MIC	=	0.78	ug.mL-1	PMID[8864235]
NPT1127	Organism	Porphyromonas gingivalis	Porphyromonas gingivalis	MIC	=	0.39	ug.mL-1	PMID[8864235]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	3300.0	nM	PMID[37578330]
NPT2	Others	Unspecified	n.a.	Inhibition	=	97.1	%	PMID[8864235]
NPT2	Others	Unspecified	n.a.	Inhibition	=	75.4	%	PMID[8864235]
NPT2	Others	Unspecified	n.a.	Inhibition	=	9.7	%	PMID[8864235]
NPT1483	Organism	Streptococcus sobrinus	Streptococcus sobrinus	MIC	=	1.56	ug.mL-1	PMID[8864235]
NPT1129	Organism	Actinomyces viscosus	Actinomyces viscosus	MIC	=	0.39	ug.mL-1	PMID[8864235]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference
Homo sapiens	n.a.	Drug uptake	=	75.65	%	PMID[17118653]
Homo sapiens	n.a.	Drug uptake	=	68.49	%	PMID[17118653]
Homo sapiens	n.a.	Drug uptake	=	69.76	%	PMID[17118653]
Homo sapiens	n.a.	Drug uptake	=	60.84	%	PMID[17118653]
Homo sapiens	n.a.	Drug uptake	=	63.15	%	PMID[17118653]
Homo sapiens	n.a.	Drug uptake	=	76.41	%	PMID[17118653]
Homo sapiens	n.a.	Drug uptake	=	56.67	%	PMID[17118653]
Homo sapiens	n.a.	Drug uptake	=	50.57	%	PMID[17118653]
Homo sapiens	n.a.	Drug uptake	=	50.42	%	PMID[17118653]
Homo sapiens	n.a.	Drug uptake	=	44.21	%	PMID[17118653]
Homo sapiens	n.a.	Drug uptake	=	40.79	%	PMID[17118653]
Homo sapiens	n.a.	Drug uptake	=	36.8	%	PMID[17118653]
Homo sapiens	n.a.	Papp	=	1.42	10^-6 cm/s	PMID[17118653]
Homo sapiens	n.a.	Papp	=	1.68	10^-6 cm/s	PMID[17118653]
Homo sapiens	n.a.	Papp	=	1.63	10^-6 cm/s	PMID[17118653]
Homo sapiens	n.a.	Papp	=	1.8	10^-6 cm/s	PMID[17118653]
Homo sapiens	n.a.	Papp	=	1.64	10^-6 cm/s	PMID[17118653]
Homo sapiens	n.a.	Papp	=	1.66	10^-6 cm/s	PMID[17118653]

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC244640 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	12455
0.1-0.2	36607
0.2-0.3	734
0.3-0.4	26
0.4-0.5	13
0.5-0.6	12
0.6-0.7	5
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC279291
1.0	High Similarity	NPC482103
1.0	High Similarity	NPC488484
1.0	High Similarity	NPC600251
0.6441	Remote Similarity	NPC488488
0.6441	Remote Similarity	NPC299734
0.6441	Remote Similarity	NPC605436
0.623	Remote Similarity	NPC482102
0.623	Remote Similarity	NPC488483
0.5738	Remote Similarity	NPC130028
0.5738	Remote Similarity	NPC474109
0.5645	Remote Similarity	NPC482107
0.5556	Remote Similarity	NPC228043
0.5556	Remote Similarity	NPC482111
0.5556	Remote Similarity	NPC482105
0.5556	Remote Similarity	NPC482104
0.5538	Remote Similarity	NPC488486
0.5538	Remote Similarity	NPC147691
0.5238	Remote Similarity	NPC488489
0.5238	Remote Similarity	NPC609387
0.5077	Remote Similarity	NPC600081

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC244640 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5219
0.1-0.2	3879
0.2-0.3	52
0.3-0.4	0
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data